


Fake It

by FamilyTrucksterImagines (oncruisecontrol)



Series: Dean Winchester Reader-Insert One Shots [5]
Category: Supernatural
Genre: F/M, Fake/Pretend Relationship, Jealous Dean, Reader-Insert, imagine
Language: English
Status: Completed
Published: 2017-08-31
Updated: 2017-08-31
Packaged: 2018-12-22 07:06:51
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,668
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11962269
Author URL: https://archiveofourown.org/users/oncruisecontrol/pseuds/FamilyTrucksterImagines
Summary: Request: Something were the reader’s not a hunter, but she’s known the Winchesters from a long time and sometimes she helps them with research. And when Sam and her pretend to date for a case, she finds herself wondering how would it feel if it were Dean’s hand holding hers instead or his voice telling her she’s beautiful. Dean’s none too happy either. They’re not in love, not yet at least, but they could be, there’s something there and they could try to make each other happy?





	Fake It

“I don’t like this,” you mumbled as you pushed the fake engagement ring onto your finger. It wasn’t that you were repulsed by the idea of pretending to be engaged to Sam – you weren’t five; you could hold a boy’s hand without being grossed out – but you were a terrible liar, and everyone had been very clear that hunting equaled danger and you should never ever do it. But Sam and Dean had begged, and swore that lives were at stake and they absolutely needed a woman’s help, because how else do you get close to a wedding planner who’d made a deal with elves, if not to hire her for your wedding?

So now you were the Future Mrs. Wylde. Mazel tov.

“We really owe you one, Y/N,” Sam said.

“No, you don’t,” you said. You’d had this conversation dozens of times over the years. You met when they saved your life, so you were always happy to help them when you could. Besides that, you were friends. You’d stopped keeping track of the favors long ago. The only difference this time was that you worried you’d fuck it up for them, and you really didn’t want that.

Two hours later, the four of you were sitting around a table while Sam talked animatedly with the wedding planner, telling her the story of how you two met and fell in love. Positive that you would mess the whole thing up if you opened your mouth, you stuck to smiling and nodding and faking giggles. Dean, the enthusiastic man of honor, was sitting next to Sam with an unconvincing smile on his face, though the wedding planner didn’t seem to notice, too caught up in the romance.

She was a nice lady. Sucked that a bunch of first born sons were being abducted and taken to Avalon to be slaves because of her.

Just as your mind was starting to drift off into the void, Sam’s hand squeezed yours a bit tighter. “You still with us, sweetie?” he asked.

Your eyebrows shot up. “Hmm? Yeah. Sorry, just, y’know, daydreaming about our big day.” Looking over at the lady, you faked a laugh, shaking your and Sam’s conjoined hands in the air. “I’m just so excited!”

Sam laughed along with you. “Aww, honey. I know the feeling. I can’t stop thinking about it, either. Gosh, I get so distracted at the office when I imagine it. Just cannot wait.” He leaned over and placed a kiss on your cheek.

“Well aren’t they just the cutest?” the wedding planner asked.

Dean’s smile grew tighter. “Oh, they sure are.”

The conversation carried on a while longer, with Sam telling the lady what kind of wedding you were thinking about: big, apparently, for both of your huge families that you totally had. Oh, and roses were your favorite. You just loved roses.

Afterwards, she let you know that she had an opening tomorrow, and you could drop by her office in the morning to really begin discussing plans. That, and you’d start owing her $50 an hour starting tomorrow. But the boys promised they’d cover that.

As soon as you got back to your place (this case being in your town, hence the decision to use you) you went back to researching fairies. As much as you loved having Sam and Dean around – genuinely – the sooner you got out of this one, the better. The boys, for their part, went straight to drinking your beer and using your Netflix.

Sam was the first to crash, or maybe just want space from his brother, and made his way to your guest room around ten, while you were still sitting in front of your books.

Dean took a seat on the other side of your desk and stared at you expectantly.

“Bored?” you asked, not looking up.

“Maybe. Or maybe I just want to talk to a friend I haven’t seen in two years.”

You smiled and flipped the book closed. “Okay. I’m open.”

“You’re not a very good fiancée,” he said, amusement evident in his voice.

“No?”

“You’re clearly not in love with Sam. Does he know?”

You laughed. “I’m only marrying him for his massive fortune. You can’t tell him, though. It could rip his heart out.”

“Ah. Lips are sealed. Hey, maybe you’ll learn to love him, huh?”

“Doubtful,” you said, narrowing your eyes and leaning forward. “He’s not my type, honestly.”

His head perked up a little, as though you’d caught his interest. “Oh really? What’s your type then?”

“I don’t know. Macho men, leather jackets, smell like whiskey.”

He laughed, and there was a little twinkle in his eye. “Huh. Never would have guessed that.”

You nodded. “Don’t get me wrong, the touchy feely stuff is great. Sam’s a good guy, and my type comes with a whole lot of assholes, but there are good things about some of ‘em, too.”

“Do tell, sweetheart.”

You bit your lip, not sure if you wanted to expand upon that, but Dean was waiting, so hell. “It’s nice having someone who looks like they could beat the crap out of anyone who lays a hand on you. It’s nice having someone who would beat the crap out of anyone who lays a hand on you. I know firsthand how scary the world is, and while I like to imagine that I’m not going to end up tied up in a vampire nest ever again, guys like you, who show up and kick ass and protect people like me, they’re comforting to have around.”

Maybe that’s why you liked guys like that; because you wanted someone who made you feel the way Dean did when he saved you. Maybe you just wanted a Dean.

Dean’s head tilted, the amusement gone – replaced by something softer.

You could feel your cheeks heating up, and wanted desperately to lighten the mood. “Plus, you know, the scruff, the dominance, it’s hot. I like hot.”

The corner of his mouth quirked up at the humor, but his eyes stayed soft, like he couldn’t shake what you’d said.

He didn’t say anything for a while, and you desperately wanted him to, so you finally said “I shared. Now it’s your turn. What’s your type, Winchester?”

His eyes met yours, and there was another moment of silence while he looked at you before answering. “Sweet girls who are patient enough to deal with jackasses like me, who smile when they see my name pop up on their phone, who are on my team, who… see me as the good guy.”

“You _are_ the good guy, Dean. You’re a good man. One of the best.”

His lips curled into a smile, and he stood from his chair, leaning over the desk to place a kiss on your forehead. “I’ll see you in the morning, sweetheart. Don’t overwork yourself, alright?”

“Yeah, alright. Night, D.”

You stayed up for a few more hours, spending most of the time actively trying not to think about the weird feeling you’d gotten in your stomach during that conversation. The clock read 1:00 when you finally dragged yourself out of your study, careful not to make too much noise as you passed by the guest room.

In the morning, you stood outside of the wedding planner’s office, this time even more nervous than yesterday, because they were actually trusting you to do a job. Admittedly, it was probably easier than lying, but it was more important than lying, and thus came with higher stakes.

“You just gotta be lookout, Y/N. Just stand there and tell Dean if she’s coming.”

You shifted on your feet nervously before Dean’s hand landed on your arm and his eyes locked on yours. “You’ll do just fine, okay? I promise.”

You bit your lip and nodded. “Okay.”

Sam took your hand before you walked in, pulling you away from Dean, which you tried not to be disappointed about. The lady greeted you brightly, glad to see ‘the happy couple’ again. The chairs in her meeting room were plush and comfortable, and you found yourself sitting next to Sam on a loveseat, with his arm around your shoulders, pulling you into leaning on him. Dean, who was on a facing yours, seemed even less interested in the conversation than he was yesterday. You tried to hide your increased discomfort as Sam was even more touchy than he had been the day before, trying to make up for your lack of input into the planning.

“So Brooklyn” – your fake name – “what kind of dress are you thinking about?”

Pulled out of your thoughts, you coughed. “Oh, uh, I was thinking of like, maybe, one with those big, uh, the tail?”

“A train.”

“That’s it. And a veil.”

Sam smiled brightly. “I can’t wait to see your face when I lift that veil, cupcake. Gosh, you’re just so beautiful.”

For some reason, your eyes darted to Dean when he said that, whose jaw shifted in… annoyance? Or was that just hopeful thinking?

Why were you hoping that Dean would be upset about Sam calling you beautiful?

And why were you wishing it was Dean who had his arm around you and was saying sweet things to you?

With that thought, now seemed as good a time as ever to start the plan and escape. “Do you have a bathroom, perhaps? I swear, coffee just goes right through me.”

The woman nodded and gave you directions and you got out of that office quicker than could be considered casual. The plan was to find her personal office and wait for Dean to join you. He was still able to see fairies, in theory, so all he had to do was come in, make sure they were there, and do the spell to send them back and you’d be done.

It took about five minutes for him to come out. “Your fiancé said he’s worried you have a stomach bug and that I should check on you,” he said. You knew he was trying to be funny, but the humor didn’t seem to reach his voice quite as much as it had before. Or maybe it did. You needed to stop overthinking things.

“That’s a lot of elves,” he mumbled, stepping into the room. “Alright, well, here goes.”

He began to recite the spell as you stood by the door, keeping watch. You could feel your hands shaking ever so slightly, nerves getting to you, certain that she’d come out and find you and kill you or something. Is that what people did?

“Alright,” he said finally, turning to you and smiling. “We did it!”

You sighed in relief. “Thank God.”

Just as he reached out for a high-five, you saw the woman step out of the meeting room and turn towards the hallway. You jumped back.

“She’s coming,” you hissed, eyes wide as you looked up at Dean. “What the hell do we do? You never told me what the escape plan was.”

He grimaced. “That’s ‘cause we forgot to think of one.”

You could hear her footsteps approaching, and you got more and more panicked with each footfall.

“Okay, uh, shit,” Dean said, glancing around. You could see on his face when an idea came to him, and suddenly he was dropping his jacket and unbuttoning the top few buttons on his shirt.

You stared at him, confused, until he grabbed you and placed you on the desk with him standing between your legs. His lips collided with yours, and one hand grabbed your leg and hoisted it up a bit to hold it against his hip. He just about forced his tongue into your mouth in order to deepen the kiss, but your mouth seemed more than willing to grant him access. You couldn’t be quite sure, but you thought you might have moaned a bit.

You’d completely forgotten what the point of this was until you heard a loud gasp behind you and Dean was pulling away, fake panic on his face. His hands moved back to his buttons, hurriedly fixing them, and you jumped off of the desk, pretending to be embarrassed. Half-pretending, actually, because this was not a moment you enjoyed being caught in.

The woman’s face turned bright red. “I am disgusted with you two,” she said. She pointed towards the hall. “Out! We are telling Jake” – Sam’s fake name – “right now!”

Your face was hot as she marched you two back to the meeting room.

Sam’s face contorted in confusion as he took in the sight of the three of you; the angry wedding planner, the blushing woman, and the smirking man with disheveled hair. (You hadn’t even noticed doing that. Jesus.)

“She’s having an affair!” The woman roared, making you jump. “With your best man!”

Sam stuttered, having no clue what to say.

“I should have known it,” she continued, “considering the way they’ve been looking at each other all day. I won’t work for you. I _don’t_ tolerate cheating.”

“That’s alright,” Sam said, putting on a fake angry voice as he stood from his chair. “The wedding’s off anyway. I’ve never felt so betrayed.”

You placed a hand over your mouth, trying to look sad while you held back a laugh. You’d crack later, you were sure.

After you were outside, Dean grinned, clearly proud of himself. “On the bright side, I sent those elves back to where they came from before making out with your fiancée.”

“That’s great,” Sam said. “But why _did_ you make out with my fiancée?”

“She was about to catch us in her office, man! We needed a cover.”

Sam looked between you two, an amused smile on his face. “Yeah, sure.”

The three of you went back to your place, and you let them know that they were free to keep crashing there until they found their next case, before you retreated back into your study. You just wanted to avoid eye contact with Dean, seeing as you were still a blushing, stuttering mess. That didn’t work for long, though, because he was back at his seat across your desk within an hour.

“I’m sorry for kissing you the way I did,” he said once you looked up at him.

You forced yourself not to frown. Of course he was. You nodded, looking away. “Yeah, D, no problem. You did what you had to do.”

He watched you, his eyebrows crinkling together. “I’m not sorry for kissing you, though.”

Your eyes snapped back to him. “Huh?”

“Ideally, I would have asked you first. Maybe been a bit gentler. Made it last a little longer.”

“I… oh,” you responded, confused.

“Stand up,” he said. It wasn’t a request, but you knew that you could have said no if you chose to.

You didn’t choose to, though. You just got up, and let him guide you until you were sitting on top of your desk with him between your legs, just as you had been earlier. His hands started on your arms and moved up to your cheeks, leaving goosebumps in their wake.

“Do you want me to kiss you, Y/N?” he asked, green eyes locked on yours.

You nodded gently. “Yes.”

He smiled for a split second, and then lowered his head until your lips connected once again. It was different this time. His lips moved against yours gently at first, the pressure building slowly. Even when his tongue made its way into your mouth, it wasn’t rough or needy. One hand stayed on your face while the other moved down to rest on your hip.

When he pulled away, that smile returned. “See? Like that.”

You smiled back. “That was nice,” you said. And then, after a minute, your hand fisted in his shirt and you pulled him back down to you in a much more heated kiss that ended up with his jacket on the floor and shirt half-way opened, just as it had been before.

**Author's Note:**

> (Find this story on Tumblr [here](https://familytrucksterimagines.tumblr.com/post/164816934106/fake-it-dean-winchester-x-reader-request).)


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